JP2886218B2 - EL device - Google Patents

EL device

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Publication number
JP2886218B2
JP2886218B2 JP1301503A JP30150389A JP2886218B2 JP 2886218 B2 JP2886218 B2 JP 2886218B2 JP 1301503 A JP1301503 A JP 1301503A JP 30150389 A JP30150389 A JP 30150389A JP 2886218 B2 JP2886218 B2 JP 2886218B2
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JP
Japan
Prior art keywords
thin film
electroluminescent device
organic
phosphor
compound
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
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JP1301503A
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Japanese (ja)
Other versions
JPH03162485A (en
Inventor
剛直 真貝
徹 並木
仁 仲田
健夫 脇本
竜史 村山
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PAIONIA KK
Original Assignee
PAIONIA KK
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Filing date
Publication date
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Priority to JP1301503A priority Critical patent/JP2886218B2/en
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Publication of JP2886218B2 publication Critical patent/JP2886218B2/en
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Description

【発明の詳細な説明】 技術分野 本発明は電界発光素子に関し、特に有機化合物を発光
体として構成される電界発光素子に関する。
Description: TECHNICAL FIELD The present invention relates to an electroluminescent device, and more particularly, to an electroluminescent device including an organic compound as a luminous body.

背景技術 この種の電界発光素子として、第2図に示すように、
陰極である金属電極1と陽極である透明電極2との間に
有機化合物からなり互いに積層された有機蛍光体薄膜3
及び有機正孔輸送層4が配された2層構造のものや、第
3図に示すように、金属電極1と透明電極2との間に互
いにい積層された有機電子輸送層5、有機蛍光体薄膜3
及び有機正孔輸送層4が配された3層構造のものが知ら
れている。ここで、有機正孔輸送層4は陽極から正孔を
注入させ易くする機能と電子をブロックする機能とを有
し、有機電子輸送層5は陰極から電子を注入させ易くす
る機能を有している。
BACKGROUND ART As this type of electroluminescent device, as shown in FIG.
An organic phosphor thin film 3 made of an organic compound and laminated on a metal electrode 1 as a cathode and a transparent electrode 2 as an anode
And a two-layer structure in which an organic hole transport layer 4 is disposed, as shown in FIG. 3, an organic electron transport layer 5 laminated between a metal electrode 1 and a transparent electrode 2, and an organic fluorescent layer. Body thin film 3
And a three-layer structure having an organic hole transport layer 4 is known. Here, the organic hole transport layer 4 has a function of facilitating the injection of holes from the anode and a function of blocking electrons, and the organic electron transport layer 5 has a function of facilitating the injection of electrons from the cathode. I have.

これら電界発光素子において、透明電極2の外側には
ガラス基板6が配されており、金属電極1から注入され
た電子と透明電極2から注入された正孔との再結合によ
って励起子が生じ、この励起子が放射失活する過程で光
を放ち、この光が透明電極2及びガラス基板6を介して
外部に放出されることになる。
In these electroluminescent devices, a glass substrate 6 is disposed outside the transparent electrode 2, and excitons are generated by recombination of electrons injected from the metal electrode 1 and holes injected from the transparent electrode 2, The exciton emits light in the process of radiation deactivation, and this light is emitted outside through the transparent electrode 2 and the glass substrate 6.

また、上述した構成の従来の電界発光素子において
は、特定の色の蛍光帯域を有するものが開発されている
が、さらにその他種々の色を発光させるべく、より多く
の種類の有機蛍光体の電界発光素子の開発が望まれてい
る。
Further, in the conventional electroluminescent device having the above-described configuration, a device having a fluorescent band of a specific color has been developed. However, in order to further emit various colors, the electric field of more types of organic phosphors is required. Development of a light emitting element is desired.

発明の概要 [発明の目的] 本発明は、上述した従来の要望を満すべくなされたも
のであって、有機蛍光体を効率良く高輝度にて発光させ
ることができる電界発光素子を提供することを目的とす
る。
SUMMARY OF THE INVENTION [Object of the Invention] The present invention has been made to satisfy the above-mentioned conventional needs, and provides an electroluminescent device capable of efficiently emitting an organic phosphor with high luminance. With the goal.

[発明の構成] 本発明による電界発光素子においては、有機化合物か
らなり互いに積層された蛍光体発光層及び正孔輸送層が
陰極及び陽極間に配された構成の電界発光素子であっ
て、前記蛍光体発光層は縮合多環化合物を含む蛍光体薄
膜からなることを特徴とする。
[Structure of the Invention] The electroluminescent device according to the present invention is an electroluminescent device having a configuration in which a phosphor emitting layer and a hole transporting layer made of an organic compound and stacked on each other are arranged between a cathode and an anode. The phosphor light emitting layer is characterized by comprising a phosphor thin film containing a condensed polycyclic compound.

以下、本発明を図に基づいて詳細に説明する。 Hereinafter, the present invention will be described in detail with reference to the drawings.

第1図は本発明の一実施例を示す構造図であり、図中
第2図及び第3図と同等部分には同一符号が付されてい
る。
FIG. 1 is a structural view showing an embodiment of the present invention, in which parts identical to those in FIGS. 2 and 3 are denoted by the same reference numerals.

図において、陰極である金属電極1には、アルミニウ
ムの1500Å膜厚の薄膜を用いる。また、陰極1には、仕
事関数が小さな金属、例えば厚さが約500Å以上のアル
ミニウム、マグネシウム、インジウム、銀又はこれらの
合金が用い得る。
In the figure, a thin film of aluminum having a thickness of 1500 ° is used for a metal electrode 1 serving as a cathode. For the cathode 1, a metal having a small work function, for example, aluminum, magnesium, indium, silver, or an alloy thereof having a thickness of about 500 ° or more can be used.

陽極である透明電極2には、インジウムすず酸化物
(I.T.O.)の2000Å膜厚の薄膜を用いる。また、陽極2
には、仕事関数の大きな導電性材料、例えば厚さが1000
〜3000Å程度のI.T.O.又は厚さが800〜1500Å程度の金
が用い得る。なお、金を電極材料として用いた場合に
は、電極2は半透明の状態となる。
For the transparent electrode 2 serving as an anode, a thin film of indium tin oxide (ITO) having a thickness of 2000 mm is used. In addition, anode 2
Have a large work function, for example, a thickness of 1000
ITO of about 3000 mm or gold with a thickness of about 800-1500 mm can be used. When gold is used as the electrode material, the electrode 2 is in a translucent state.

金属電極1と透明電極2との間には、図の上から順に
積層された有機蛍光体薄膜7及び有機正孔輸送層4が配
されている。
Between the metal electrode 1 and the transparent electrode 2, an organic phosphor thin film 7 and an organic hole transport layer 4 which are laminated in order from the top of the figure are arranged.

有機正孔輸送層4には、トリフェニルアミン誘導体、
例えば下記式(I)の化合物の薄膜を用いる。
The organic hole transport layer 4 includes a triphenylamine derivative,
For example, a thin film of the compound of the following formula (I) is used.

また、有機正孔輸送層4には、更に下記式(II)〜
(XII)のCTM(Carrier Transmiting Materials)とし
て知られる化合物を用い得る。
The organic hole transport layer 4 further includes the following formulas (II) to (II).
A compound known as CTM (Carrier Transmitting Materials) of (XII) may be used.

有機蛍光体薄膜7としては、縮合多環化合物を含む蛍
光体薄膜が用いられる。かかる有機蛍光体薄膜7の膜厚
は1μm以下に設定される。
As the organic phosphor thin film 7, a phosphor thin film containing a condensed polycyclic compound is used. The thickness of the organic phosphor thin film 7 is set to 1 μm or less.

さらに、有機蛍光体薄膜としては、下記構造式(A1)
〜(A7)で示される縮合多環化合物が用いられる。
Further, as the organic phosphor thin film, the following structural formula (A1)
The condensed polycyclic compounds represented by (A7) to (A7) are used.

但し、上記構造式(A1)のナフタレン化合物中、R1,R
2,R3及びR4は独立に、水素,カルボキシル基,アミノ
基,水酸基またはスルホ基(但し、アルキル成分は好ま
しくは、炭素原子数が1〜5個であるが、6個以上でも
よい)である。
However, in the naphthalene compound of the above structural formula (A1), R 1 , R
2 , R 3 and R 4 are each independently hydrogen, a carboxyl group, an amino group, a hydroxyl group or a sulfo group (however, the alkyl component preferably has 1 to 5 carbon atoms, but may have 6 or more carbon atoms) It is.

この蛍光体薄膜を形成する縮合多環化合物(A1)は、
第1表の官能基のNo.1〜No.3の組み合わせを有するもの
が好ましい。
The condensed polycyclic compound (A1) forming the phosphor thin film is
Those having a combination of No. 1 to No. 3 of the functional groups in Table 1 are preferable.

但し、上記構造式(A2)のアントラセン化合物中、
R5,R6及びR7は独立に、水素,ハロゲン,アリール基,
アルキル基,不飽和鎖式炭化水素から誘導される1価の
基,アニシル基またはアセトオキシ基(但し、アルキル
成分は好ましくは、炭素原子数が1〜5個であるが6個
以上でよく、アリール成分は好ましくは、炭素原子数が
6〜14個であるが、18個以上でもよい)である。
However, in the anthracene compound of the above structural formula (A2),
R 5 , R 6 and R 7 are independently hydrogen, halogen, aryl,
An alkyl group, a monovalent group derived from an unsaturated chain hydrocarbon, an anisyl group or an acetoxy group (however, the alkyl component preferably has 1 to 5 carbon atoms, but may have 6 or more carbon atoms; The component preferably has 6 to 14 carbon atoms, but may have 18 or more).

この蛍光体薄膜を形成する縮合多環化合物(A2)は、
第2表の官能基のNo.4〜No.27の組み合わせを有するも
のが好ましい。
The condensed polycyclic compound (A2) forming this phosphor thin film is
Those having a combination of No. 4 to No. 27 of the functional groups in Table 2 are preferable.

但し、上記構造式(A3)のフルオレン化合物中、R8
びR9独立に、アミノ基またはニトロ基である。
However, in the fluorene compound of the structural formula (A3), R 8 and R 9 are independently an amino group or a nitro group.

下記式(A3−28)のフルオレン化合物が好ましい。 A fluorene compound represented by the following formula (A3-28) is preferred.

上記構造式(A4−29)に示すように、R10がアミノ基
であるフルオラテン化合物も用いられる。
As shown in the above structural formula (A4-29), a fluorathene compound in which R 10 is an amino group is also used.

但し、上記構造式(A5)のテトラセン化合物中、R11,
R12,R13,R14及びR15は独立に、水素,カルボキシル基,
アミノ基,水酸基またはスルホ基(但し、アルキル成分
は好ましくは、炭素原子数が1〜5個であるが、6個以
上でもよい)である。
However, in the tetracene compound of the structural formula (A5), R 11 ,
R 12 , R 13 , R 14 and R 15 are independently hydrogen, a carboxyl group,
An amino group, a hydroxyl group or a sulfo group (however, the alkyl component preferably has 1 to 5 carbon atoms, but may have 6 or more carbon atoms).

下記式(A5−30)のテトラセン化合物が好ましい。 A tetracene compound represented by the following formula (A5-30) is preferred.

但し、上記構造式(A6)のピレン化合物中、R16,R17,
R18及びR19は独立に、水素,カルボキシル基,アミノ
基,水酸基,スルホ基またはスルホニウム基(但し、ア
ルキル成分は好ましくは、炭素原子数が1〜5個である
が、6個以上でもよい)である。
However, in the pyrene compound of the above structural formula (A6), R 16 , R 17 ,
R 18 and R 19 are independently hydrogen, a carboxyl group, an amino group, a hydroxyl group, a sulfo group or a sulfonium group (however, the alkyl component preferably has 1 to 5 carbon atoms, but may have 6 or more carbon atoms. ).

この蛍光体薄膜を形成する縮合多環化合物(A6)は、
第3表に官能基のNo.31〜No.34の組み合わせを有するも
のが好ましい。
The condensed polycyclic compound (A6) forming this phosphor thin film is
Those having a combination of functional groups No. 31 to No. 34 in Table 3 are preferable.

但し、これら縮合多環化合物(A7−38)及び(A7−3
9)であるコロネン及びデカシクレンも用いられる。
However, these fused polycyclic compounds (A7-38) and (A7-3
9) Coronene and dekacyclene are also used.

また、上記電界発光素子においては陰極1及び陽極に
2間に有機蛍光体薄膜7及び有機但孔輸送層4を配した
2層構造としたが、従来の陰極1及び蛍光体薄膜7層間
に例えば下記(XX)式のペリレンテトラカルボキシル誘
導体からなる有機電子輸送層5を配した3層構造として
も同様の効果を奏する。
Further, in the above-mentioned electroluminescent device, the organic phosphor thin film 7 and the organic hole transporting layer 4 are arranged between the cathode 1 and the anode 2 in a two-layer structure. Similar effects can be obtained with a three-layer structure in which an organic electron transport layer 5 made of a perylene tetracarboxyl derivative of the following formula (XX) is provided.

発明の効果 以上説明したように、本発明による電界発光素子にお
いては、有機化合物からなり互いに積層された蛍光体発
光層及び正孔輸送層が陰極及び陽極間に配された構成の
電界発光素子であって、蛍光体発光層は縮合多環化合物
を含む蛍光体薄膜からなるので、低電圧にて効率良く高
輝度赤色発光させることができる。
Effect of the Invention As described above, the electroluminescent device according to the present invention is an electroluminescent device having a configuration in which a phosphor luminescent layer and a hole transport layer made of an organic compound and stacked on each other are arranged between a cathode and an anode. Since the phosphor light-emitting layer is formed of a phosphor thin film containing a condensed polycyclic compound, high-luminance red light can be efficiently emitted at a low voltage.

実 施 例 本発明の実施例の電界発光素子を作成しそれを発光さ
せた。
EXAMPLE An electroluminescent device according to an example of the present invention was prepared and emitted light.

まず、ガラス基板上に陽極である透明電極のI.T.O.を
2000Å膜厚で成膜したものを用意した。陰極である金属
電極1には、アルミニウムを用いた。
First, a transparent electrode ITO, which is the anode, was placed on a glass substrate.
A film having a thickness of 2000 mm was prepared. Aluminum was used for the metal electrode 1 serving as the cathode.

有機正孔輸送層4には、上記(I)式のトリフェニル
アミン誘導体を用いた。
For the organic hole transport layer 4, a triphenylamine derivative of the above formula (I) was used.

有機蛍光体薄膜7としては、上記(A7−39)式のデカ
シクレンを用いた。
As the organic phosphor thin film 7, decacyclene represented by the above formula (A7-39) was used.

正孔輸送層、蛍光体薄膜及び陰極を成膜する際の真空
度、蒸着速度及び膜厚等の成膜条件は第4表の如くであ
り、この表において得られた電界発光素子に電圧を印加
することにより得られた発光特性を併記する。
The film forming conditions such as the degree of vacuum, the deposition rate and the film thickness when forming the hole transport layer, the phosphor thin film and the cathode are as shown in Table 4, and the voltage is applied to the electroluminescent device obtained in this table. The emission characteristics obtained by applying the voltage are also shown.

【図面の簡単な説明】[Brief description of the drawings]

第1図は本発明の実施例を示す構造図、第2図及び第3
図は従来例を示す構造図である。 主要部分の符号の説明 1……金属電極(陰極) 2……透明金属(陽極) 4……有機正孔輸送層 6……ガラス基板 7……有機蛍光体薄膜
FIG. 1 is a structural view showing an embodiment of the present invention, FIG. 2 and FIG.
FIG. 1 is a structural view showing a conventional example. Description of Signs of Main Part 1 Metal electrode (cathode) 2 Transparent metal (anode) 4 Organic hole transport layer 6 Glass substrate 7 Organic phosphor thin film

───────────────────────────────────────────────────── フロントページの続き (72)発明者 脇本 健夫 埼玉県入間郡鶴ヶ島町富士見6丁目1番 1号 パイオニア株式会社総合研究所内 (72)発明者 村山 竜史 埼玉県入間郡鶴ヶ島町富士見6丁目1番 1号 パイオニア株式会社総合研究所内 (56)参考文献 特開 昭61−55183(JP,A) 特開 昭54−75485(JP,A) Amalytica.Chemica acta,215,1988,p341−345 Jpn.J.Appl.Phys.L etters.Vol.27,No.2, 1988,p269−271 Indian J.pure.App l.Phys.,Vo.14,1976、p 345−347 (58)調査した分野(Int.Cl.6,DB名) C09K 11/06 CA(STN) REGISTRY(STN) WPI(DIALOG)──────────────────────────────────────────────────続 き Continued on the front page (72) Inventor Takeo Wakimoto 6-1, 1-1 Fujimi, Tsurugashima-cho, Iruma-gun, Saitama Prefecture (72) Inventor Tatsufumi Murayama 6, Fujimi, Tsuruga-machi, Iruma-gun, Saitama No. 1 in the Research Laboratory of Pioneer Corporation (56) References JP-A-61-55183 (JP, A) JP-A-54-75485 (JP, A) Amarytica. Chemica acta, 215, 1988, p341-345 Jpn. J. Appl. Phys. Letters. Vol. 27, No. 2, 1988, pp. 269-271 Indian J. et al. pure. Appl. Phys. , Vo. 14, 1976, p 345-347 (58) Fields investigated (Int. Cl. 6 , DB name) C09K 11/06 CA (STN) REGISTRY (STN) WPI (DIALOG)

Claims (2)

(57)【特許請求の範囲】(57) [Claims] 【請求項1】有機化合物からなり、互いに積層された蛍
光体発光層及び正孔輸送層が陰極及び陽極間に配された
構成の電界発光素子であって、前記蛍光体発光層は下記
構造式(A3) (上記式(A3)中、R8及びR9独立に、アミノ基またはニ
トロ基である)で示されるフルオレン化合物を含む蛍光
体薄膜からなることを特徴とする電界発光素子。
1. An electroluminescent device comprising an organic compound, wherein a phosphor light emitting layer and a hole transport layer laminated on each other are arranged between a cathode and an anode, wherein the phosphor light emitting layer has the following structural formula (A3) (In the formula (A3), R 8 and R 9 are independently an amino group or a nitro group.) An electroluminescent device comprising a phosphor thin film containing a fluorene compound represented by the formula:
【請求項2】有機化合物からなり互いに積層された蛍光
体発光層及び正孔輸送層が陰極及び陽極間に配された構
成の電界発光素子であって、前記蛍光体発光層は下記構
造式(A4) で示されるフルオランテン化合物を含む蛍光体薄膜から
なることを特徴とする電界発光素子。
2. An electroluminescent device having a structure in which a phosphor light emitting layer and a hole transport layer made of an organic compound and stacked on each other are arranged between a cathode and an anode, wherein the phosphor light emitting layer has the following structural formula ( A4) An electroluminescent device comprising a phosphor thin film containing a fluoranthene compound represented by the formula:
JP1301503A 1989-11-20 1989-11-20 EL device Expired - Fee Related JP2886218B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP1301503A JP2886218B2 (en) 1989-11-20 1989-11-20 EL device

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP1301503A JP2886218B2 (en) 1989-11-20 1989-11-20 EL device

Publications (2)

Publication Number Publication Date
JPH03162485A JPH03162485A (en) 1991-07-12
JP2886218B2 true JP2886218B2 (en) 1999-04-26

Family

ID=17897698

Family Applications (1)

Application Number Title Priority Date Filing Date
JP1301503A Expired - Fee Related JP2886218B2 (en) 1989-11-20 1989-11-20 EL device

Country Status (1)

Country Link
JP (1) JP2886218B2 (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE69511755T2 (en) * 1994-04-26 2000-01-13 Tdk Corp Phenylanthracene derivative and organic EL element
ATE358169T1 (en) * 1999-09-30 2007-04-15 Idemitsu Kosan Co ELECTROLUMINESCENT ORGANIC DEVICE
JP3969941B2 (en) * 2000-09-01 2007-09-05 三洋電機株式会社 Organic light emitting device
EP1437395B2 (en) * 2002-12-24 2015-08-26 LG Display Co., Ltd. Organic electroluminescent device
US7651788B2 (en) 2003-03-05 2010-01-26 Lg Display Co., Ltd. Organic electroluminescent device
KR101311942B1 (en) * 2009-12-31 2013-09-26 제일모직주식회사 Aromatic ring-containing compound for resist underlayer, and resist underlayer composition

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
Amalytica.Chemica acta,215,1988,p341−345
Indian J.pure.Appl.Phys.,Vo.14,1976、p345−347
Jpn.J.Appl.Phys.Letters.Vol.27,No.2,1988,p269−271

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JPH03162485A (en) 1991-07-12

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